Sodium Carbonate → 6-(3-Hydroxyphenyl)-2-(4-phenoxyphenyl) pyrazolo[1,5-a]pyrimidine-3-carbonitrile

HRID 64376

Reaction equation

Br[C:2]1[CH:3]=[N:4][C:5]2[N:6]([N:8]=[C:9]([C:13]3[CH:18]=[CH:17][C:16]([O:19][C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=4)=[CH:15][CH:14]=3)[C:10]=2[C:11]#[N:12])[CH:7]=1.[OH:26][C:27]1[CH:28]=[C:29](B(O)O)[CH:30]=[CH:31][CH:32]=1.C([O-])([O-])=O.[Na+].[Na+]>O1CCOCC1.O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[OH:26][C:27]1[CH:32]=[C:31]([C:2]2[CH:3]=[N:4][C:5]3[N:6]([N:8]=[C:9]([C:13]4[CH:18]=[CH:17][C:16]([O:19][C:20]5[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=5)=[CH:15][CH:14]=4)[C:10]=3[C:11]#[N:12])[CH:7]=2)[CH:30]=[CH:29][CH:28]=1

Participants

Conditions

Temperature: 65 °C

Procedure

To a solution of 6-bromo-2-(4-phenoxyphenyl)pyrazolo[1,5-a]pyrimidine-3-carbonitrile (782 mg, 2.0 mmol) in dioxane (10 mL) and H2O (10 mL) was added 3-hydroxyphenylboronic acid (276 mg, 2.0 mmol), Pd(PPh3)4 (240 mg, 0.2 mmol) and Na2CO3 (424 mg, 4.0 mmol). After stirring at 65° C. under N2 for 16 hr, the mixture was concentrated and 100 mL of DCM, 10 mL of CH3OH, 100 mL of H2O were added. Organic layers were separated from aqueous layers and dried over Na2SO4 and purified by chromatography column on silica gel eluting with DCM/CH3OH to afford 500 mg (62%) of 6-(3-hydroxyphenyl)-2-(4-phenoxyphenyl) pyrazolo[1,5-a]pyrimidine-3-carbonitrile as a yellow solid. MS (ESI) m/e [M+1]+ 404.9.

Workup

concentrationthe mixture was concentrated
addition100 mL of DCM, 10 mL of CH3OH, 100 mL of H2O were added
customOrganic layers were separated from aqueous layers
dry with materialdried over Na2SO4
custompurified by chromatography column on silica gel eluting with DCM/CH3OH

Sources & evidence

ORD record: ord-ef099b0ab4d746cc97e8ec35a5a8e201
Source dataset: uspto-grants-2016_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09447106B2

Linked notes

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